Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±)Tolterodine

Gaurav Goswami; Navya Chauhan; Abhijit Mal; Subhomoy Das; Mowpriya Das; Manas K. Ghorai

doi:10.1021/acsomega.8b02487

Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±)Tolterodine

Gaurav Goswami
, Navya Chauhan
, Abhijit Mal
, Subhomoy Das
, Mowpriya Das
, Manas K. Ghorai

Department of Chemistry
Indian Institute of Technology Kanpur

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

A simple synthetic route to access racemic 3,3-disubstituted propylamines in excellent yields (up to 95%) via Lewis acid catalyzed S_N2-type ring opening of activated azetidines with electron-rich arenes and heteroarenes under mild conditions has been accomplished. The methodology is efficiently used for the racemic synthesis of an antimuscarinic drug, tolterodine, in four steps in 47% overall yield.

Original language	English
Pages (from-to)	17562-17572
Number of pages	11
Journal	ACS Omega
Volume	3
Issue number	12
DOIs	https://doi.org/10.1021/acsomega.8b02487
State	Published - 18 Dec 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

Funding

M.K.G. is grateful to IIT-Kanpur for financial support. G.G. and N.C. thank UGC, India, for research fellowships.

Funders
IIT-Kanpur
University Grants Committee

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10.1021/acsomega.8b02487

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abstract = "A simple synthetic route to access racemic 3,3-disubstituted propylamines in excellent yields (up to 95\%) via Lewis acid catalyzed SN2-type ring opening of activated azetidines with electron-rich arenes and heteroarenes under mild conditions has been accomplished. The methodology is efficiently used for the racemic synthesis of an antimuscarinic drug, tolterodine, in four steps in 47\% overall yield.",

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AU - Goswami, Gaurav

AU - Chauhan, Navya

AU - Mal, Abhijit

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AU - Das, Mowpriya

AU - Ghorai, Manas K.

PY - 2018/12/18

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Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±)Tolterodine

Abstract

Bibliographical note

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